Synthesis of α,β-Unsaturated Acylsilanes via Perrhenate-Catalyzed Meyer–Schuster Rearrangement of 1-Silylalkyn-3-ols

Abstract

We report the synthesis of α,β-unsaturated acylsilanes via the perrhenate-catalyzed Meyer-Schuster rearrangement of 1-silylalkyn-3-ols. Propargylic alcohols derived from TES-acetylene and substituted benzaldehydes can be converted to acylsilanes using a combination of p-TSA·H(2)O and n-Bu(4)N·ReO(4), or Ph(3)SiOReO(3) in good yields. Some propargylic alcohols derived from ketones, as well as aliphatic and unsaturated aldehydes, can also be converted to acylsilanes; however, they were often prone to side reactions.